Tobacco Chemistry. 40. Syntheses of (12R,13R)- and (12S,13S)-8,12-Epoxy-14-labden-13-ol and (13R)- and (13S)-8,13-Epoxy-14-labden-12-one, Four Tobacco Diterpenoids.

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Abstract
Two of the title compounds, [from Nicotiana tabacum], (12R, 13R)- and (12S, 13S)-8,12-epoxy-14-labden,13-ol (9, 10) were obtained as major products on peracid oxidation of (12Z)-abienol, a reaction also furnishing small amounts of (12R, 13R)- and (12S, 13S)-8, 13-epoxy-14-labden12-ol which were converted to the other 2 title compounds (13R)- and (13S)-8,13-epoxy-14-labden-12-one, by oxidation using Jones'' reagent. The stereostructures of 9 and 10 were determined by X-ray analysis of (12R)-14,15-bisnor-8,12-epoxylabdane-13-one prepared by oxidative degradation of the 8, 12-epoxyalcholol (9), and by consideration of the reaction mechanism involved in the peracid oxidation. 13C NMR data for the synthetic and some related compounds are given and the effects of steric factors on their 13C shieldings are discussed.

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